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Ch_322b_18.15 - Chapter 18.15 lecture note

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Amides from Carboxylic Acid Anhydrides Analogous reactions occur between acid anhydrides and ammonia or amines. CH 3 COCCH 3 O = O = acetic anhydride + 2 NH 3 CH 3 CNH 2 O = + CH 3 CO NH 4 O = - + acetamide ammonium acetate by way of CH 3 C-OCCH 3 O = O = + :NH 3 CH 3 C-N-H O = H H + + CH 3 CO 2 - nucleophilic attack at acyl carbon :NH 3 CH 3 CNH 2 O = + NH 4 +
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Cyclic acid anhydrides react in a similar way: C C O = O = O phthalic anhydride + 2 NH 3 H 2 O warm C C O = O = NH 2 ONH 4 - + ammonium phthalamate H + H 2 O C C O = O = NH 2 OH phthalamic acid (81%) neutralization Vigorous heating results in dehydration and formation of the important compound phthalimide . C C O = O = NH 2 OH phthalimide (~100%) 150-160 o C C C O = O = NH K a = 5 x 10 -9 + H 2 O Imides have the general structure: C N C O = O =
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Amides from Esters Esters undergo nucleophilic substitution at the acyl carbon with nitrogen nucleophiles such as ammonia ( ammonolysis ) or amines ( amination ). CH 3 COC 2 H 5 O = ethyl acetate + :NH 3 H 2 O ammonolysis CH 3 CNH 2 + C 2 H 5 OH O = acetamide
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Amides from Carboxylic Acids Carboxylic acids react with aqueous ammonia to produce
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